Hydrolysis Mechanism of N-(benzoyl)-C-(N-methylanilino)imidoylchloride Derivatives

N-(benzoyl)-C-(N-methylanilino)imidoylchloride 유도체의 가수분해 반응메카니즘

  • 권기성 (충남대학교 자연과학대학 화학과) ;
  • 이용구 (충남대학교 자연과학대학 화학과) ;
  • 성낙도 (충남대학교 농과대학 농화학과) ;
  • 김천석 (한국인삼연초연구소)
  • Published : 1993.06.20

Abstract

Rate constants of hydrolysis of N-(benzoyl)-C-(N-methylanilino)imidoylchlorides were determined by UV spectrophotometry in 50% (v/v) aqueous methanol at 25$^{\circ}C$. On the basis of rate equation, substituent effect, solvent effect, salt effect, thermodynamic parameters and hydrolysis product analysis, it may be concluded that the hydrolysis of N-(benzoyl)-C-(N-methylanilino)imidoylchlorides proceed through $S_N$1 mechanism via azocarbonium ion intermediate in the range of from pH 3.0 to pH 10.0, while above pH 10.0 and below pH 3.0 the hydrolysis proceeds through nucleophilic addition-elimination (A$d_{N-E}$) mechanism.

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References

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